10 Things to Do in Chicago at Night

Within the United States, Chicago is known as The Second City, because it has always been as important as New York, but in some ways has grown in its shadow. For this reason, its nightlife has created an identity just as interesting as that of the major cultural capitals of the planet and there are plenty of things to see and do in Chicago morning, noon and night.

I invite you to continue reading this compilation of activities to get a better idea of the things you could do on your trip after the sun drops below the horizon and the temperatures drop rapidly.

Can you imagine driving through Chicago in a bus shaped like a keg, stopping to sample different types of beer at craft breweries?

Beer's influence on Chicago dates back to the 19th century, and not even Prohibition in the 1920s prevented the brewing of beer from continuing: under a façade of legal shops and shops, beer was brewed and sold clandestinely, and even today it's still a hallmark of the Windy City.

Delicate flavours, others more forceful and even some extravagant. Among the beers you can sample on this original tour are Dovetail Helles, Metropolitan Flywheel and Begyle Blonde Ale, so there's something for everyone!

The Chicago River alone is one of the most visited spots in the entire city because of the many bridges that span it from north to south to connect the Chicago Loop section of the financial district with the area known as the Near North Side.

This geographical importance has made it a favourite tourist destination when it comes to quiet, family-friendly overnight plans in Chicago, so the city has used this to its advantage by creating all kinds of nighttime tours on the waters of this most famous of rivers.

Most Chicago evening cruises on the Chicago River tend to last a maximum of 1 hour as it's a relatively short stretch, although some offer dinner and live music and consequently last much longer.

The food that is crowned the queen of local Chicago dining is undoubtedly the Deep Dish Pizza, a pizza that is prepared in a deep dish panwith several layers of mozzarella on top of the dough just below the sauce that would traditionally separate the two elements.

Throughout the city you will find pizzerias offering a more traditionalist version of the Deep Dish Pizza as well as more innovative versions that incorporate other foods that are not historically associated with what is expected of this recipe with Italian origins.

However, Chicago food tours are an excellent option if you're looking to enjoy several establishments so that you can reach a verdict on which of the restaurants you liked the most at the end of your trip.

Cities that are full of skyscrapers like Chicago offer a unique night scene because the streets are illuminated hundreds of metres upwards by the many lights that these tall buildings usually have.

At night you have the opportunity to see the city from a different perspective with night tours that usually take place throughout the financial and tourist centre of the city. Some are designed for pedestrians, while others are designed to be done in a vehicle, just like the best Chicago tour buses: double-decker buses in which the second level is completely uncovered and are accompanied by a guide or audio guide to help you understand the historical importance of the area you are visiting.

In addition, many of these tours can also deal with very specific topics about this community, such as the stories of the mafias of the mid-century or tours that focus on enjoying the city's railway history.

The Chicago Cubs are this city's most important baseball team and in their more than 150 years of history have become one of the cultural pillars of this community.

Their MLB games are played at Wrigley Field, an important stop on the itinerary of tourists interested in the sports culture of the destinations they visit.

The MLB regular season starts in early spring and ends in mid-fall, so if you're in town during any of these months it's highly recommended that you add a Chicago Cubs game to your evening plans in the Windy City, as games are usually played around 8pm and can last two hours or even two and a half hours.

Few cities have as strong a comedy presence as Chicago and without a doubt this city is the epicentre of entertainment in the English-speaking comedy industry.

Tina Fey, Steve Carell, Eugene Levy, Amy Pohler or Stephen Colbert are just some of the personalities who started their careers in comedy in Chicago, so it's a great idea to check out some of the nightly shows if you're looking for entertainment after sundown.

In this sense, one show I recommend you don't miss if you're in the mood for a good laugh is a Shakespeare performance at The Lounge. It's a fun performance called "Drunk Shakespeare" in which the novels of the English writer are mixed with an improvised performance by an actor in a state of inebriation. As you read it! You'll have a very entertaining time with this play, which is considered one of the best in its field.

If you want to enjoy a spectacular night view during your visit to Chicago, you have plenty of alternatives.

The Ellis Tower, completed in 1974, was the tallest building in the world for a couple of years and for another decade it remained the tallest skyscraper in the United States. Today, with its Skydeck and glass cubicles, it remains one of the best options for enjoying the Windy City skyline.

• The observation deck is open every day of the week.
• Tickets can be booked until 9 pm.
• During busy periods, such as summer and Christmas, special opening hours are available until 10 or 11 pm.

Meanwhile, the 360 Observation Deck in Chicago is another ideal alternative for those who are looking for a spectacular night scene more than 300 metres above this beautiful city and stands out for the degree of visibility so complete that it offers its visitors.

• It is located at 875 North Michigan Avenue, formerly known as the John Hancock Center.
• It is open until 11 pm on Fridays and Saturdays.

Boystown, also known as Northalsted, is the quintessential LGBT neighbourhood in Chicago. Its historical significance is due to the fact that it functioned as a sort of social haven for the entire Midwestern community in the 1960s and 1970s.

As you can imagine, nightlife activities abound throughout this area that stretches north and south between W Grace Street and W Belmont Avenue. There are bars, cafes, nightclubs, trendy boutiques and a wide range of comedy clubs. If you're on the streets you're guaranteed to have a good time.

The Annoyance Theatre is one of the city's most iconic comedy clubs, but if you're in the area and it's crowded you can also visit the Trickery or the Laugh Factory. Keep in mind that any entertainment alternative in the neighbourhood will be quite unique and in general this community is known for the warmth with which tourists are welcomed.

In many American cities it has been quite common for immigrant communities to form neighbourhoods to reside and establish businesses under the aesthetic and community values they had in their countries of origin.

Chicago's Greektown is an excellent example and is an area that to this day has maintained its essence and has all kinds of restaurants serving authentic Hellenic food. If you're looking for an entertaining and quality place to dine in Chicago, but want to go for a more unique experience, you can head to Greektown for a cultural experience that unites America with the best of the Greek identity.

Chinatown is another immigrant community that is relatively close to Greektown. For a more extensive dining experience, head south on I-90 and in less than 10 minutes without traffic you'll be in another of the city's most interesting neighbourhoods.

Navy Pier is an unmissable stop on your visit to Chicago if you really want to see the city's most important attractions. In fact, it attracts some 9 million visitors annually and nighttime is one of the best times to visit because of the colourful lighting that characterises it.

It's an excellent family plan that is included among the things to see and do in Chicago with children because of the Ferris wheel and other mechanised rides such as a carousel.

If you visit, you can't miss an authentic Chicago-style Hot Dog and I guarantee you'll also love the views it offers over the illuminated panorama of the city's waterfront over Lake Michigan in the dark of night.

Going out at night or going out during the day in Chicago are two virtually identical situations as there are no associated risks after dark in a city with such a significantly high police presence.

The only recommendation I can give you is to be aware that the underground system closes its doors at around 1:30 am and reopens at 4:00 am or 5:00 am on Sundays. Therefore, it's always a good idea to have cash to pay for a taxi back to the hotel, although most taxis in the city nowadays have credit card payment machines.

Weather is another factor to consider when going out at night in Chicago. Winters and autumns are characteristically much colder than in other US cities because of the wind in this Great Lakes region, so a coat is a necessity, while in the summer it's best to go outside in breathable clothing because the high daytime temperatures can leave an environmental after-effect at night.